I think one angle to consider is instead of learning how to manage, learn how to own and then adapt that to become a co-host.Something like owners work/hire you to pick up slack in regards to being a "on the ground" person to handle problems.

If you never intend on selling, no problem, but if you do my recommendation is to have your exit option very clearly laid out and a good lawyer to draft it up. 

That does not add up.

This does not apply to my flip property which would not come up under my personal history since it is titled in an entity name, not me personally.Suggestions? 

Based on what I have heard/read thus far, it seems like I don't need a formal legal structure such as LLC for running this is as an active business (but I may set up an LLC for asset protection, which is allowed by my mortgage lender).

If the property has continued to appreciate, perhaps him buying you out at market value makes the most sense, then take the cash and roll into a new property.It sounds like you would like him to pick up another $500/month (pay you the $1,000/mo rent + pay 50% of the remaining mortgage split). 

Neighbors can have legitimate complaints or they can make up stuff out of jealousy or for political reasons to cause you headaches. 

Without cash flow you will end up going out of pocket for any repairs and Capex expenses. 

Well thanks for clearing that up @Russell Brazil!

If the house went up $200K in 3 years (even assuming you bought it for $1.3M), you are now going to have to pay taxes on that when you sell.